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From $368 per night (USD)
VRBO
2 Bedroom Townhome in the Key West Golf Club
Bedrooms:
3
Bathrooms:
2
Sleeps:
5
**Beautiful 2-Bedroom Townhome in Key West Golf Club** Welcome to this charming 2-bedroom, 2.5-bathroom townhome locate ...
From $368 per night (USD)
VRBO
From $2727 per night (USD)
VRBO
Galleon | Hot Tub | Marina | Lux Resort | Concierge
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
The Galleon Resort is a premier destination in Key West, Florida, offering an unbeatable combination of luxury, comfort, ...
From $2727 per night (USD)
VRBO
From $1502 per night (USD)
VRBO
Sunset Harbor | Hyatt | Hot Tub | Pool | Marina | Lux Resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1502 per night (USD)
VRBO
From $2371 per night (USD)
VRBO
Sleeps 6 | Hyatt | Lux Resort | Concierge | Pool | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Set along the stunning Atlantic Ocean, Hyatt Windward Pointe Resort seamlessly blends Key West’s laid-back vibe with mod ...
From $2371 per night (USD)
VRBO
From $1207 per night (USD)
VRBO
Sunset Harbor | Marina | Hot Tub | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1207 per night (USD)
VRBO
From $2803 per night (USD)
VRBO
Parrot Key | Beachfront | Kitchen | Hot Tub | Pool
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Step into a paradise of white sands and glimmering pools, where boat drinks and watersports are just steps away at Parro ...
From $2803 per night (USD)
VRBO
From $1234 per night (USD)
VRBO
The Banyan | Concierge | Beach Access | Pool
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Located in the heart of historic Old Town Key West, The Banyan Resort is a charming escape set on a mid-1800s estate ste ...
From $1234 per night (USD)
VRBO
From $728 per night (USD)
VRBO
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $728 per night (USD)
VRBO
From $1598 per night (USD)
VRBO
Coconut Beach | Beach | Concierge | Pool | Gym
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Coconut Beach Resort transports you to your very own private oasis, where the charm of old island architecture meets lus ...
From $1598 per night (USD)
VRBO
From $1918 per night (USD)
VRBO
Hyatt Beach | Concierge | Spa | Pool | Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary at Hyatt Beach House Resort, where the lush landscapes of Key West meet unparalleled l ...
From $1918 per night (USD)
VRBO
From $2903 per night (USD)
VRBO
Galleon | Marina | Concierge | Hot Tub | Spa
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Nestled along the sparkling Gulf of Mexico in historic Old Town, The Galleon Resort places you in the heart of Key West’ ...
From $2903 per night (USD)
VRBO
From $1951 per night (USD)
VRBO
Sunset Harbor | Hyatt | Marina | Concierge | Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your serene oasis in the heart of Key West’s iconic Old Town, where lush greenery and contemporary design cre ...
From $1951 per night (USD)
VRBO
From $1238 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠𝐌𝐞𝐢𝐥𝐢 Near Duval Street, Waterfront Sunset Harbor Resort. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! 🌅 Nestled in the he ...
From $1238 per night (USD)
VRBO
From $340 per night (USD)
Expedia
3 Bedroom 2 Bathroom Near Beaches and Art Galleries
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Spacious 3-Bedroom, 2-Bathroom Retreat in Key West Escape to paradise in this charming Key West rental, perfectly situa ...
From $340 per night (USD)
Expedia
From $1046 per night (USD)
VRBO
𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢 Dream Getaway at the Beach House Resort+Amenities. 2BR
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to 𝐅𝐢𝐧𝐝𝐢𝐧𝐠 𝐌𝐞𝐢𝐥𝐢🌴 Experience Key West Paradise at the Beach House Resort Retreat! 🏖️ Additional $ ...
From $1046 per night (USD)
VRBO
From $5625 per night (USD)
VRBO
Key West Florida Charming 1-bedroom resort with WiFi, AC
Bedrooms:
1
Bathrooms:
1
Sleeps:
6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
VRBO
From $5625 per night (USD)
VRBO
Key West Studio Charming resort with WiFi, AC, fitness room
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
VRBO
From $5625 per night (USD)
VRBO
Hyatt Beach House Resort Key West 2-bedroom with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to your private sanctuary in the lush landscape of Key West. Imagine old-fashioned screen-enclosed porches, gard ...
From $5625 per night (USD)
VRBO
From $5625 per night (USD)
VRBO
Key West Hyatt Charming 2-bedroom resort with WiFi, AC
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a serene oasis nestled in the heart of Key West’s historic Old Town. Surrounded by lush greenery, this retrea ...
From $5625 per night (USD)
VRBO
From $634 per night (USD)
VRBO
Casa Marina Tropical Oasis
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Discover this 2-bedroom gem in Key West. This welcoming house boasts two gorgeous king bedrooms, ensuring a tranquil sta ...
From $634 per night (USD)
VRBO
$Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool$
From $270 per night (USD)
VRBO
Helluva Happy Place | Escape to Old Town Key West - 3 bed\/2.5 bath townhome with private pool
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Escape to Old Town Key West and indulge in a monthly retreat at our charming 3-bedroom, 2.5-bathroom townhome. Nestled i ...
From $270 per night (USD)
VRBO
From $479 per night (USD)
Expedia
ROYAL POINCIANA COTTAGE - Quaint Old Town location
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Royal Poinciana is a studio cottage with a queen bed, kitchen ,and private bath. The queen bed sleeps 2 people and the k ...
From $479 per night (USD)
Expedia
From $614 per night (USD)
VRBO
Oceanfront Splendor @ the Key West Beach Club
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
29 NIGHT MINIMUM RENTAL ... This property is not allowed to accept pets. Enjoy endless views of the tranquil waters of ...
From $614 per night (USD)
VRBO
From $233 per night (USD)
VRBO
In the heart of Old Town lies the HAVEN HOUSE
Bedrooms:
2
Bathrooms:
1
Sleeps:
2
Haven House provides the perfect home base to be near the center of everything but be able to retreat to home and watch ...
From $233 per night (USD)
VRBO
From $478 per night (USD)
VRBO
The Hideout! Where Luxury Meets Location. Fully Renovated, with Pool.
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
Welcome to The Hideout, where luxury meets location. Look no further than "The Hideout" for upscale luxury and single- ...
From $478 per night (USD)
VRBO
$Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -$
From $645 per night (USD)
VRBO
Life is a Breeze at Windward Breeze by RENT KEY WEST VACATIONS - 2\/2 townhome -
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. Ther ...
From $645 per night (USD)
VRBO
From $1573 per night (USD)
VRBO
Relax in Style at Windsor Townhomes #4
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1573 per night (USD)
VRBO
From $1392 per night (USD)
VRBO
MERMAID COVE - A collection of four units on Duval
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Mermaid Cove features four separate units (two cottages and two apartments), each with a private entrance and all decora ...
From $1392 per night (USD)
VRBO
$THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome$
From $547 per night (USD)
VRBO
THALIA'S RETREAT @ Duval Square 2bd\/2ba townhome
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parkin ...
From $547 per night (USD)
VRBO
From $1653 per night (USD)
VRBO
No secrets at Pilar's Secret - Just a great location!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Pilar’s Secret is hidden away in the heart of Old Town Key West just half a block off the famous Duval Street. This secl ...
From $1653 per night (USD)
VRBO
From $383 per night (USD)
VRBO
Deckside Suite - Efficiency at its finest!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Efficiency at its finest! The Deckside Suite is the perfect vacation rental in Key West for those who are trying to get ...
From $383 per night (USD)
VRBO
$Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval$
From $1696 per night (USD)
VRBO
Windsor Townhomes #6 - Large pool 3B\/3.5 bath, 3 blocks to Duval
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Elegance and modern sophistication are apparent as you enter any one of these six conveniently located townhomes in a q ...
From $1696 per night (USD)
VRBO
From $431 per night (USD)
VRBO
Rent at PORCHSIDE PARADISE - Steps to Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Porchside Paradise is located in the front section of the Conch Republic Cottages. This beautiful home-away-from-home fe ...
From $431 per night (USD)
VRBO
$Mid Town 2\/1 TREE HOUSE RETREAT$
Click For Pricing
Expedia
Mid Town 2\/1 TREE HOUSE RETREAT
Bedrooms:
1
Bathrooms:
2
Sleeps:
6
Tree House Retreat is located on the second floor of Amanda's Garden Getaway. It offers a large living room with french ...
Click For Pricing
Expedia
$Amanda's Garden Getaway - Mid Town 3\/2 cottage$
From $1155 per night (USD)
VRBO
Amanda's Garden Getaway - Mid Town 3\/2 cottage
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Lush tropical grounds and large shared pool are just outside the doors of the Garden Getaway. Expansive covered porch, l ...
From $1155 per night (USD)
VRBO
$Mid Town Affordable 3bd\/2.5ba 3 story Townhome$
From $791 per night (USD)
Expedia
Mid Town Affordable 3bd\/2.5ba 3 story Townhome
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Coco's Hideaway is a 3-level townhome that is part of a mini-compound complete with lush tropical gardens and a huge sha ...
From $791 per night (USD)
Expedia
From $585 per night (USD)
VRBO
Half block to Duval @ Mango Hideaway -studio apt
Bedrooms:
1
Bathrooms:
1
Sleeps:
3
The Mango Hideaway is comfortable junior suite, with sofa sitting area with adjoining king bedroom. The suite features ...
From $585 per night (USD)
VRBO
$ALOHA - Large 1 level 4bd\/4ba Monthly Rental$
From $587 per night (USD)
VRBO
ALOHA - Large 1 level 4bd\/4ba Monthly Rental
Bedrooms:
4
Bathrooms:
4
Sleeps:
10
Aloha is a stunning private residence on corner lot in the Casa Marina District. Updated 2 years ago, this beautiful hom ...
From $587 per night (USD)
VRBO
$Eyebrow Suite - 2bd\/1.5ba Suite off Duval$
From $698 per night (USD)
VRBO
Eyebrow Suite - 2bd\/1.5ba Suite off Duval
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Eyebrow Suite is a spacious two-bedroom suite with one of the best locations on the island. Its large front porch and pa ...
From $698 per night (USD)
VRBO
$Spacious Townhome on Windsor Lane 3\/3.5$
From $1708 per night (USD)
VRBO
Spacious Townhome on Windsor Lane 3\/3.5
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
Welcome to Windsor Townhomes #3! Once you enter this beautifully decorated oasis…your vacation begins. This townhome has ...
From $1708 per night (USD)
VRBO
From $296 per night (USD)
VRBO
ESPERANZA SUITE Monthly Rental close to Duval
Bedrooms:
2
Bathrooms:
1
Sleeps:
4
Esperanza Suite is a bi-level suite with a very spacious upstairs king bedroom with a writing desk and chair and a color ...
From $296 per night (USD)
VRBO
From $512 per night (USD)
Expedia
ROBINSON CRUSOE COTTAGE - Quaint poolside cottage on Margaret St
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Robinson Crusoe Cottage is a one-bedroom cottage with a queen bed, sleeper sofa, kitchen, and private bath. The queen be ...
From $512 per night (USD)
Expedia
$ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental$
From $284 per night (USD)
VRBO
ANNA MARIA HAVEN - Renovated 3bd\/3ba Conch Monthly rental
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
This newly remodeled Conch house is located on Olivia Street in Old Town Key West just two and a half blocks from World ...
From $284 per night (USD)
VRBO
From $940 per night (USD)
Expedia
Escape to the wonderful Cuban Paradise!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Built in 1917 as a “club” for Cuban cigar makers and their families as their home-away-from-home, this building soon bec ...
From $940 per night (USD)
Expedia
$Tropical Village: The Southern Cross - Quiet & gated. Pool\/Porch\/Pet friendly$
From $586 per night (USD)
VRBO
Tropical Village: The Southern Cross - Quiet & gated. Pool\/Porch\/Pet friendly
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
There are stars in the southern sky! The Southern Cross takes its name from the “crux” constellation that guided sailors ...
From $586 per night (USD)
VRBO
From $1614 per night (USD)
Expedia
The Caroline House Estate - 1 Block off Duval & Key West Historic Seaport
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
This gorgeous classical Key West Estate property is quite possibly the most stylish blend of historic Victorian-Caribbea ...
From $1614 per night (USD)
Expedia
From $1578 per night (USD)
VRBO
A contemporary island gem that was formerly used as a bottling plant,
Bedrooms:
3
Bathrooms:
3
Sleeps:
8
A contemporary island gem that was formerly used as a bottling plant, this modern and spacious home is now a desirable t ...
From $1578 per night (USD)
VRBO
From $345 per night (USD)
VRBO
Key West at Ocean’s Corner!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Whether you want to explore the historic sites, enjoy the nightlife, or relax in nature, you’ll find it all during your ...
From $345 per night (USD)
VRBO
$Escape to \Oasis on 18th\ w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary$
From $571 per night (USD)
VRBO
Escape to \"Oasis on 18th\" w\/ PRIVATE HEATED Pool in the KW Golf Club Sanctuary
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Escape to your own private paradise at "Oasis on 18th," a luxurious three-bedroom, three-bathroom haven nestled within t ...
From $571 per night (USD)
VRBO
From $271 per night (USD)
VRBO
Last Mango Beach Retreat
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Experience the allure of La Brisa Penthouse! Step into this captivating two-bedroom, two-bathroom condo nestled within t ...
From $271 per night (USD)
VRBO
From $495 per night (USD)
VRBO
Beach Club #112 - Unique Oceanfront living
Bedrooms:
2
Bathrooms:
2
Sleeps:
5
Unique oceanfront living only 65 feet from the Atlantic! The Key West Beach Club is a quiet, peaceful residential build ...
From $495 per night (USD)
VRBO
From $2001 per night (USD)
VRBO
Key West, Galleon Resort, Marina, In Town, Pool, Hot Tub
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to The Galleon Resort in Key West, where paradise meets luxury at the southernmost tip of the United States. In ...
From $2001 per night (USD)
VRBO
From $1374 per night (USD)
VRBO
Sunset Harbor Resort & Spa, In Town, Marina, Hot Tub.
Bedrooms:
1
Bathrooms:
1
Sleeps:
4
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1374 per night (USD)
VRBO
From $1588 per night (USD)
VRBO
Sunset Harbor Resort & Spa, Hot Tub, Pool
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Discover this relaxing oasis in the heart of Key West's famed Old Town. Lush, verdant foliage surrounds the grounds and ...
From $1588 per night (USD)
VRBO
$Escape to \Casa Escondida\$
From $605 per night (USD)
VRBO
Escape to \"Casa Escondida\"
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Escape to the enchanting "Casa Escondida," a historic Conch Style home with a modern twist, nestled on a tranquil, seclu ...
From $605 per night (USD)
VRBO
$SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!$
From $599 per night (USD)
Expedia
SWEET DREAMS ARE MADE OF 'THE KEYS' ~ Bahama Village 2 BR\/2 Ba Home w\/ Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BAHAMA VILLAGE BEAUTY... This dream of a home is yours for the ultimate escape to southernmost paradise! Located in the ...
From $599 per night (USD)
Expedia
From $529 per night (USD)
VRBO
POCKETFUL OF SUNSHINE ~Gorgeous 5 BR Near Beach and Prime Fireworks Watching!
Bedrooms:
6
Bathrooms:
5
Sleeps:
10
EXQUISITE MODERN FAMILY COMPOUND... If a large home with all the modern luxuries is a must for your next island getaway, ...
From $529 per night (USD)
VRBO
$THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!$
From $314 per night (USD)
Expedia
THE NEST ~ Charming Conch Cottage Close to the Beach and Duval w\/ Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
HIDDEN GEM... The perfect location for guests who want to walk and bike to everything Key West has to offer. Modern cot ...
From $314 per night (USD)
Expedia
$SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!$
From $282 per night (USD)
VRBO
SWEET LIKE SUMMERTIME ~ 3 BR\/2Ba Home w\/ Pool and Yard!
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
CLASSIC UPDATED CHARMER... Welcome to this beautifully renovated 3 bedroom 2 bath pool home, located in the heart of Bah ...
From $282 per night (USD)
VRBO
From $1424 per night (USD)
VRBO
Waterfront Sunset Harbor Resort Near Old Town+Amenities: 2BR FindingMeili
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Welcome to FindingMeili🌴 Experience Paradise at Hyatt Vacation Club at Sunset Harbor! An Additional Savings from $500 ...
From $1424 per night (USD)
VRBO
$Spacious 2\/2 Waterfront Condo w\/Pool&Dock$
From $948 per night (USD)
VRBO
Spacious 2\/2 Waterfront Condo w\/Pool&Dock
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Summary: Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip a ...
From $948 per night (USD)
VRBO
$OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!$
From $658 per night (USD)
Expedia
OASIS SOUTH~Stunning 5 BR\/3 Ba w\/ Pool!
Bedrooms:
3
Bathrooms:
7
Sleeps:
14
BRING THE WHOLE GANG... If you and your large band of loved ones are looking for the perfect gathering in southernmost ...
From $658 per night (USD)
Expedia
$McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!$
From $525 per night (USD)
VRBO
McCartney's Manor - Deluxe K Suite W\/Pvt. Spa!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Cool pastel, Caribbean inspired decor with original art throughout by Robin Hix. Bose speaker, Alexa Echo, full kitche ...
From $525 per night (USD)
VRBO
$CHANGES IN LATITUDES ~ Renovated 3 BR\/2.5 Ba Home w\/ Pool!$
From $583 per night (USD)
Expedia
CHANGES IN LATITUDES ~ Renovated 3 BR\/2.5 Ba Home w\/ Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
MODERN MERGES WITH HISTORIC CHARM... Discover a blend of sleek contemporary elegance that interweaves with the rich tape ...
From $583 per night (USD)
Expedia
From $250 per night (USD)
VRBO
Charming + Circa 1889 Historic Eyebrow Home
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
28 Night Minimum. Welcome to "The Saltbox"! Featured in design magazines. 710 Ashe Street is a charming house circa 18 ...
From $250 per night (USD)
VRBO
Click For Pricing
Expedia
Ocean view apartment on coconut resort
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Coconut Beach Resort once belonged to the late Senator John Spottswood. He originally purchased the property because of ...
Click For Pricing
Expedia
From $249 per night (USD)
VRBO
CASA DE CANAL ~ 3 BR, 2 Ba. Canal Front Home!
Bedrooms:
2
Bathrooms:
3
Sleeps:
8
KEY WEST BOATER'S BONANZA... This waterfront gem is a dream for boating and fishing enthusiasts. Indulge in all your nau ...
From $249 per night (USD)
VRBO
From $240 per night (USD)
VRBO
Old Town Key West Live like a local
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Live like a local! This vacation flat is located at Mile marker 1, and sits nestled above the street right on Truman Av ...
From $240 per night (USD)
VRBO
From $476 per night (USD)
VRBO
THE GOOD LIFE ~ Charming 2nd Floor 1 Bedroom, 1 Bath Truman Annex Condo!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
COZY VALUE IN TRUMAN ANNEX… This 2nd Floor one bedroom, one bath condo is located in The Shipyard, a neighborhood of the ...
From $476 per night (USD)
VRBO
From $159 per night (USD)
Expedia
ANCHORS AWAY ~ Cheerful 1 BR, 1 Ba Condo with Private Hot Tub in The Meadows!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
CLASSIC AND COZY... Exhale your worries away as you approach this delightful condo, one of four that are situated insid ...
From $159 per night (USD)
Expedia
From $592 per night (USD)
VRBO
GARDEN HIDEAWAY ~ Beautiful lush landscaped oasis located in the Casa Marina!
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
PARADISE AWAITS... This charming home is located in one of the most desirable locations in Key West, Casa Marina. Garden ...
From $592 per night (USD)
VRBO
From $166 per night (USD)
Expedia
CABIN FEVER ~ First Floor 1 Bedroom, 1 Bathroom with Full Kitchen and Pool!
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
SIMPLISTIC ELEGANCE... Enjoy easy island living in this quaint and cozy Key West gem located in the attractive community ...
From $166 per night (USD)
Expedia
From $145 per night (USD)
VRBO
Mango Tree Key West Cottage
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
True Key West flavor! 1 Bedroom 1 Bathroom apartment newly remodeled and updated Conch House located on White St.with h ...
From $145 per night (USD)
VRBO
From $1016 per night (USD)
Expedia
Craig & Cindy's 4 Bedroom Key West Truman Annex Porter House with private pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bedrooms and a private ...
From $1016 per night (USD)
Expedia
From $1030 per night (USD)
VRBO
JUST OFF DUVAL~ 2nd Floor Condo in Center of Duval St. with Parking Space!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
STEPS TO DUVAL ST… Take advantage of this premier opportunity to indulge in all your desired Key West bucket list items ...
From $1030 per night (USD)
VRBO
From $1011 per night (USD)
VRBO
Hyatt Residence Club - Key West, FL - 2 Bedroom Unit - Beach House Location!!!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Experience a tropical getaway designed in classic Key West style, o ering manicured gardens and panoramic views of the G ...
From $1011 per night (USD)
VRBO
From $991 per night (USD)
VRBO
💲 HUGE DISCOUNT for 28 day OCEAN FRONT! 90 FT BALCONY💰
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Please contact the owner for stays less than 28 days before you try to book. Military Vouchers are Welcome! In Key We ...
From $991 per night (USD)
VRBO
From $1024 per night (USD)
VRBO
Rose Lane Villas - Villa Aqua - 2 King Bedrooms - Downtown Key West
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Nestled on a quiet lane in the heart of Old Town Key West, Rose Lane Villas is as close to the action as you'll get with ...
From $1024 per night (USD)
VRBO
From $521 per night (USD)
VRBO
Enjoy More Privacy in a Truman Annex End Unit Townhome
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Contact us about special Summer Rates! Absolute Best Location! Our Townhome is set in the tranquil verdant gardens of ...
From $521 per night (USD)
VRBO
From $816 per night (USD)
VRBO
Hyatt Sunset Harbor, overlooking the Gulf of Mexico.
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
<p>Close to snorkeling, ecotours, and more, this smoke-free condo brings it all within reach. There's convenient onsite ...
From $816 per night (USD)
VRBO
From $759 per night (USD)
VRBO
Key West Beachside Spacious Two Bedroom Condo in the Top Location on the Key
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to our Key West Condo, the Key West Cabana. This spacious well appointed 2 bedroom, 2 full bath condo that’s ri ...
From $759 per night (USD)
VRBO
$\Tranquility \ At Ann Street Gardens Steps From Duval$
From $1133 per night (USD)
VRBO
\"Tranquility \" At Ann Street Gardens Steps From Duval
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Location is ideal for this wonderful one bedroom retreat. A lush, inviting compound created so owners and guests could e ...
From $1133 per night (USD)
VRBO
Click For Pricing
VRBO
Craig & Cindy Truman Annex Foundry Townhouse 2 bedrooms 2.5 baths
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Craig & Cindy Truman Annex Foundry Townhouse is a 2 bedroom 2 1/2 bath townhouse in the best location in all of Key West ...
Click For Pricing
VRBO
From $311 per night (USD)
VRBO
Mojitoville: 3 bedroom pet-friendly, Old Town, Private Pool, Historic Seaport
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Mojitoville is perfect for the discriminating guest who wants to enjoy close proximity to Key West's Historic Seaport wi ...
From $311 per night (USD)
VRBO
From $758 per night (USD)
VRBO
Quintessential Key West Resort! Hyatt Windward Pointe two bedroom. Best rates!
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
<p>You'll find bicycles, golfing, and more on site at this smoke-free condo. Fort East Martello Museum and Gallery is wi ...
From $758 per night (USD)
VRBO
From $281 per night (USD)
VRBO
SMATHER'S BEACH, Deluxe 2 BR oceanview unit, GREAT RATES ,
Bedrooms:
2
Bathrooms:
2
Sleeps:
6
Oceanfront at Smathers Beach in beautiful Key West, Florida. Why pay for a hotel, when you can enjoy your own private o ...
From $281 per night (USD)
VRBO
$Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking$
From $2064 per night (USD)
VRBO
Location In Down Town Key West W\/ 2 Pools, Huge Private Roof Deck & Parking
Bedrooms:
7
Bathrooms:
7
Sleeps:
16
Perfect location and great for entertaining! In the heart of Old Town Key West just steps from restaurants, bars, theate ...
From $2064 per night (USD)
VRBO
From $878 per night (USD)
Expedia
TIDES ON SIMONTON ~ Perfectly located just off Duval and all the fun!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
ADORING RETREAT ONE BLOCK FROM DUVAL… One bedroom gem on Simonton Street one block from Duval. Totaling one bedroom, on ...
From $878 per night (USD)
Expedia
$BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!$
From $230 per night (USD)
VRBO
BONITA EN ROSA ~ Charming 2 Bedroom, 1 Bathroom Home w\/ Pool!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $230 per night (USD)
VRBO
$LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!$
From $159 per night (USD)
Expedia
LA PUERTA PEQUENA ~ Charming 1 Bedroom, 1 Bathroom w\/ Loft in Old Town!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $159 per night (USD)
Expedia
$PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!\$
From $373 per night (USD)
VRBO
PINEAPPLE BREEZE ~ JUST RENOVATED Home in The Meadows with Pool!\"
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
PICTURE PERFECT PARADISE... This newly renovated 3 bedroom, 2 bathroom retreat is nestled in the highly sought-after, hi ...
From $373 per night (USD)
VRBO
From $169 per night (USD)
Expedia
SEAPORT SANCTUARY ~ Come and Enjoy this Romantic & Lovely Couples Hideaway!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
A QUIET BUNGALOW IN THE HISTORIC SEAPORT... Private one bedroom home in the heart of Old Town. A great place for a coup ...
From $169 per night (USD)
Expedia
From $430 per night (USD)
VRBO
SEAHORSE COVE ~ Tropical Luxury Located In The Heart Of Old Town Key West!
Bedrooms:
2
Bathrooms:
3
Sleeps:
4
FLAWLESS SETTING, PERFECT LOCATION… Tucked away on a hidden lane right in the middle of Old Town, this luxurious private ...
From $430 per night (USD)
VRBO
$GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!$
From $2713 per night (USD)
Expedia
GOOD VISIBILITY ~ 4 Bedroom, 3 Bathroom Condo w\/ Pool and Ocean Views!
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
YOUR OCEANFRONT OASIS AWAITS... This remarkable and magical retreat is sure to provide all the R & R you need to refresh ...
From $2713 per night (USD)
Expedia
From $559 per night (USD)
VRBO
THE SEASHELL ~ Classic, Luxury Old Town Gem with Private Pool & Gardens!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
**Please note that this rental only allows for payment by check/E-check. Credit card payment will be subject to additio ...
From $559 per night (USD)
VRBO
From $686 per night (USD)
Expedia
The Most Perfect Old Town Key West Location for a Retreat!
Bedrooms:
3
Bathrooms:
4
Sleeps:
12
The home (also known as Margaux's Hideaway) was built in 1890's, with a farmhouse charm, and porches off of every bedroo ...
From $686 per night (USD)
Expedia
From $326 per night (USD)
VRBO
HEMINGWAY'S HIDEOUT ~ Historic Old Town Cottage with Pool!
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
ISLAND TIME AWAITS… Step up to this serene, tropical cottage inviting you in with a multitude of swaying palms, a privat ...
From $326 per night (USD)
VRBO
$SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!$
From $1950 per night (USD)
Expedia
SAPODILLA HOUSE ~ Spectacular 3B\/3.5Ba Annex Home w\/Private Heated Pool!
Bedrooms:
4
Bathrooms:
3
Sleeps:
6
PREMIER TROPICAL RETREAT... Come spoil yourself in this conveniently located two-story home tucked away on a quiet lane ...
From $1950 per night (USD)
Expedia
From $849 per night (USD)
VRBO
IN GOOD SPIRITS ~ Waterfront Condo, Wrap-Around Balcony & Community Pool!
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
BEACHES ON BOTH SIDES... This two bedroom condo is close to the airport, beaches, restaurants and minutes away from Duva ...
From $849 per night (USD)
VRBO
From $239 per night (USD)
Expedia
SEAS THE DAY~ Newly Built Townhome in Perfect Location with Community Pool!
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
IMMACULATE RETREAT JUST STEPS FROM IT ALL... Beautifully designed and decorated townhouse located in the Southernmost Ca ...
From $239 per night (USD)
Expedia

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